Family-friendly vacation rentals in Northwest Side

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Northwest Side

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 343 reviews

Lovely, bright, 3-bedroom Avondale flat. Private.

3 bedroom apartment perfect for families or groups of 3-5 people. Transportation is accessible with many CTA bus stops nearby, the Kennedy expressway only minutes away, and two Blue line stations less than a 15 minutes walk. The newly redecorated apartment is located on a quiet street in the up-and-coming Avondale neighborhood with free street parking (parking permit will be provided). Only a few minutes away from Logan Square, amazing restaurants, nightlife, and entertainment are easy to find.

Sep 16 – 23

R3,169 ZAR per night

Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 427 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Oct 17 – 24

R2,299 ZAR per night

Superhost

Apartment in Chicago

4.9 out of 5 average rating, 283 reviews

Modern Logan Square Apartment, steps from train!

The apartment is close to Logan 11 Bar, The Boiler Room, The Chicago Diner: Logan Square, Revolution Brewery, Cafè Mustache. You’ll love the place because of the location, the neighborhood, transport convenience (30 second walk), Divvy bikes accross street, 606 elevated path amongst countless other things to check out. Travelers, families, & big group welcome but It's NOT a place to host parties, please not that it can be rather noisy because of the bar downstairs. By train 15mins downtown.

Apr 19 – 26

R2,554 ZAR per night

Guest favorite

Guest suite in Chicago

4.97 out of 5 average rating, 237 reviews

Stylish Studio in Historic Logan Square

Brand new, unique garden studio (4 steps down), located in the heart of the highly desirable Logan Square neighborhood. This luxurious space with heated floors & a spa inspired bathroom is situated on the Historic Logan Boulevard, 2 blocks from the CTA Blue Line which runs between downtown & O'Hare airport. The suite has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Convenience & excitement are easily accessible!

Sep 25 – Oct 2

R2,937 ZAR per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Sep 8 – 15

R2,549 ZAR per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 119 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

Private entrance apartment on the 2nd floor of this historic bungalow. Free street parking! Medicinal & recreational smokers permitted... outdoor ONLY. This comfortably cozy quiet get-away is nestled in NW Portage Park in a family neighborhood. Dog and kids park nearby. Fenced yard for Fido. Backyard patio w/ BBQ grill. High-speed internet. Front porch swing Easy access to buses & Jefferson Park Transit train station to Downtown & Museum Campus NO PARTIES

Nov 29 – Dec 6

R2,204 ZAR per night

Guest favorite

Apartment in Logan Square

4.89 out of 5 average rating, 339 reviews

Sunny Logan Square Artists' home

2nd floor classic Chicago 2flat with lots of light. 3 bedrooms available, with 2 additional sofabeds. Great if you and family/group of friends are in town for an event and want to stay together. Grocery store 1.5 blocks away. Quiet street. Parking is decent. New bath has all marble walls, extra long/deep tub and rain shower. 1 mile walk to the Logan Square CTA Blue Line and Logan Square brunch/night-life. 5 min walk to Metra. Walk to 606 trail.

Dec 1 – 8

R2,104 ZAR per night

Guest favorite

Bungalow in Chicago

4.84 out of 5 average rating, 152 reviews

Your Cozy 2nd Home!/Near Rosemount /O'Hare Airport

O'Hare Airport 14 mins/6 miles to downtown/9+mins-All-State Arena, D.Stephen Convention Rosemont Theater & Village Park Entertainment District.Bus stop 25 ft. Free street Parking. If you love a cozy place & a well-spaced single-family home w/ an excellent neighborhood this place is for you. Free parking is available along the street and is never an issue.

Jun 3 – 10

R2,965 ZAR per night

Guest favorite

Apartment in Logan Square

4.96 out of 5 average rating, 219 reviews

Spacious apartment in Logan Square

Ideal location 2 blocks from beautiful Palmer Square Park and short walk to Logan Boulevard. Enjoy the many great restaurants and bars in the neighborhood. Take a stroll or a bike ride on the 606 elevated path. One bedroom with queen size bed. Large open floor plan and air mattress for extra guests. Easy access to public transportation.

Oct 22 – 29

R3,506 ZAR per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 490 reviews

2BR Bursting w/ Character in Hip Logan Square!

The unit sits on our extra wide city lot in the center of hip Logan Square! The apartment is eclectic and well decorated, with vintage touches and full of charm. For a garden unit it feels spacious, clean, bright and comes with all of the desired amenities, including access to our spacious side yard!

Mar 26 – Apr 2

R2,653 ZAR per night

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 419 reviews

Cozy, Quiet, Garden Getaway!

Quiet 1BD garden apartment in Northcenter/Lincoln Square. 10 minutes to the el and Lincoln Square, one of the best neighborhoods in Chicago. Full kitchen, bathroom, cable and internet. Tree lined street close to two parks and a river walk. ****WE DO NOT RENT TO FILM CREWS****

Mar 19 – 26

R1,970 ZAR per night

Guest favorite

Apartment in Lincoln Square

4.78 out of 5 average rating, 269 reviews

Cozy Garden-Subterranean Apartment

Our cozy Lincoln Square one bedroom apartment sleeps 2, has a fully furnished kitchen, and is close to Lincoln square shops and great restaurants/carry-out. Ample street parking & close to public transportation. Entrance to the apartment at back of building.

Sep 13 – 20

R1,979 ZAR per night